


Helping Out

by MrTwilight



Category: Original Work
Genre: Anal Sex, Deepthroating, F/M, Oral Sex, POV First Person, Rimming, Rough Sex, Sexual Experimentation, Sibling Bonding, Sibling Incest, Strap-Ons, Underage Sex, Vaginal Sex
Language: English
Status: Completed
Published: 2018-05-10
Updated: 2018-05-10
Packaged: 2019-05-04 18:29:27
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 2,826
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14599089
Author URL: https://archiveofourown.org/users/MrTwilight/pseuds/MrTwilight
Summary: After being called to the Principal office for no apparent reason, he walks to his mom's office to find out she was pulling a prank on him as she just wanted to tell him that she wasn't going to be home for two days and his older sister was going to take care of him. After failing to go out with his mom to delay going home, he goes home to find out that his sister has a thing for him and dreams of doing things to him.





	Helping Out

“Delvin Ross, Report to my office immediately.” My principal said with frustration in her voice.

“Someone is busted.” A boy said as I looked at the door in worry, making a few people giggle.

“Enough of that.” My teacher said with a smile.

I stood up and walked to her office. Once I got there, I peeked in through the door to see her working on paperwork. I took a deep breath as I opened the door and walked in.

“Is something the matter mom?” I asked nervously, making her look at me with a serious stare, then she smiled.

“No honey.” She said with a giggle. “I’m just messing with you. I was hoping to tell you that your sister will be babysitting you for the weekend and was hoping you wouldn’t mind.”

“Really mom, you make me nervous for that?” I growled, making her giggle with a nod. “Unbelievable.”

“I’m sorry, did I overdo it?” She asked with a grin.

“You know you did.” I said, making her giggle again.

“There's one more thing.” She said. “You are grounded.”

“Not funny mom.” I said.

She stared at me blankly, then I saw a twitch in her eye as she was holding back a laugh that she was desperately trying to hide from me.

“Nice try mom, you’re going to have to do better than that.” I said, making her giggle. “Why are you messing with me?”

“Because I'm board.” She said with a grin. "And your my favorite student."

I whined and walked out of the room, making her laugh.

“Wait honey, take this before I forget.” She said.

I looked back and saw her holding out fifty dollars, making me walk to her.

"Is this for a pizza?" I asked.

“No, it’s your allowance.” She said.

I nodded and grabbed it.

“Can we take a detour before I go home?” I asked.

“You finally got a friend?” She asked with hope on her face, making me stare at her in worry, then her face fill with disappointment. “And I thought you managed to one up your sister with something again.”

“Wait, she don't have a friend either?” I asked.

“From what I'm hearing.” She said as she nodded.

“Well I can be her friend if you want.” I said, making her smile.

“It's not the same honey.” She said. “What is your detour?”

“I was hoping we could eat together before you leave.” I said.

“Really a date with me?” She asked with a grin, making me stare at her in discomfort. “I was kidding honey. Yes, we can if it don't take too long.”

“Your choice.” I said. “I haven’t thought that far yet, I'm planning as I go.”

“Are you trying to delay going home?” She asked.

“Yes.” I said with a smile. “It’s so boring there.”

She smiled and nodded.

“Fine, I’ll think of something.” She said. “Meanwhile you need to think of hobbies to do at home.”

“If that was even possible.” I mumbled.

“Are you saying we need to move?” She asked.

“No of course not, that would make your life a living hell.” I said, making her smile.

“Not exactly.” She said. “I have been watching the house just down the road from the school.”

“I won't stop you if you want it.” I said.

The last bell rung, making her look to the clock.

“Crap, I couldn’t think of anything in that short of time.” She whined.

“Maybe you should have pulled your prank a little sooner.” I said, making her smile. “I’ll be in the car.”

“No honey, just take the bus home, I have way too much work to do.” She said. “I didn't realize how late it was.”

I sighed and walked out of the school. Once I was home, I opened the door and walked to my room, but before I got there, I heard my sister talking to someone, making me look to her closed door.

“Damn it why can’t I get off on this crap.” She growled as I cracked the door, then walked in as I saw she was alone and looking at a book. Once I got to her, I saw it wasn’t just any book, but a porn magazine.

“Damn it, I can’t believe I have to revert to my old shameful habits.” She whined.

A second later, she growled as she reached for a drawer, then pulled out a picture of me naked on my bed, making me stare in disbelief. I peeked over her shoulder to see she really was masturbating to me, making me smile as I didn't know she was into me.

“You know you could have just asked.” I said, making her scream and punch me in the face as everything went black.

“Oh god, oh god.” My sister cried in panic as I felt something wet touching my face. “Please don't hate me little brother. I can't believe I messed up your beautiful face.”

A second later, she felt around my cheek bone, then I moaned as my head started to pound, making me open my eyes to see her cleaning my face with worry on her face.

“I’m so sorry for knocking you out.” She whined. "Please don't be mad that I gave you a bruise."

"It was my fault for entering without permission.” I said.

“I gave you permission to enter any time you wish.” She said.

“How did you get that picture of me?” I asked.

She smiled nervously, but didn't say anything, then she glanced at my crotch.

“When did you start liking me like that?” I asked, making her smile turn to a small grin as she bit her lip, but still said nothing.

I looked to her crotch and saw she was still half naked, making me take a deep breath and reach for her slit. Her face filled with worry as she saw my nervousness.

“Don’t do it if you really don't want to.” She said as she grabbed my hand.

“I’ll do anything to make you happy.” I said. “I even told mom that I would be your friend since she told me you don't have one, but I didn't tell her that I’m willing to go this far.”

“How could she possibly know that?” She asked.

I shrugged my shoulders, then reached up to her breast with my other hand, making her stare at me in disbelief as I felt around.

“You don't have a friend to do this with?” She asked.

“I’m too shy to do this to anyone else.” I said. “I trust you with my life.”

She smiled in worry.

“You do realize that this isn't legal.” She said.

“That’s if anyone finds out.” I said with a smile, making her bite her lip again. “Now can you tell me how you got that picture? I don't sleep naked. I might start now that i know you like me like this.”

Her face filled with color as she liked that idea.

"Please tell me." I said. "I won't get angry."

“I kinda took it when I was planning to… Um... molest you, from not being able to get off on this crap.” She said nervously. “I didn't go through with it though since my nerves became jumbled up.”

I smiled as I unbuttoned my pants, making her look down to what I was doing, then back to my face in disbelief.

“Do you want to take over?” I asked, making her face fill with color.

She grabbed my hand and pulled it away, then she picked me up and took me to my room.

“Why my room?” I asked."Your bed is bigger.”

“I want you to feel like you're in your turf.” She said as she laid me down on my bed. “I don't want you getting scared.”

“That’s not possible with you.” I said. “Do every fantasy you have for me. I don't care what you do to me, well don't do anything with pee or shit. That’s just gross.”

She giggled as she nodded in agreement.

“I don't think you want me to do all my fantasies on you.” She said.

“I’ll tell you if I don't like it.” I said.

She stared at me for a second, then nodded as she left the room and came back with a box, making me stare at it in confusion.

“What’s that?” I asked.

“My fantasies.” She said, then pulled out an eight inch pink strapon, making me laugh in disbelief.

“When did you get that thing?” I yelp from being startled from the size of the thing, then I looked at her in worry. “You weren't planning to go lesbian, were you?”

“No, this was all for you the day I made that picture.” She said.

I smiled nervously.

“Still wanting to go with my fantasies?” She asked, making me stare at the large dildo.

“Just go easy on me.” I said.

“Yes, of course.” She said as she pulled out a ball gag, making me stare at it in discomfort.

“That’s sorta a turn off, but do as you wish to me.” I said. “This is for you after all.”

“It’s not a must.” She said as she put it back in the box, then set it on the floor next to the bed, making me look in it, but she pushed me flat and started to take off my clothes.

I stared at her as she glanced at my face nervously.

“Are you into me to?” She asked.

“I’m willing to try out anything at least once.” I said, making her smile.

“Kinda wish I knew that earlier.” She said as she started to pull off my pants, then she stared at my small mound that was under my underwear.

“How are you not hard?” She asked.

“First time maybe.” I said nervously.

“No don’t be nervous.” She said. “I won't judge.”

She placed her hand on me and woke up my shaft with her tender touch, then she smiled as she started to grab it. Once I was fully hard, she bit her lip as she pulled it through the hole.

“Damn, you’re bigger than I imagined.” She said, making me giggle, then she got down and started to suck me.

I grunted as I fell flat, making her look at me, then grabbed my hands and placed them on her head as she pushed me into her throat.

“Oh god.” I moaned.

A few minutes of her sucking me, I lifted my head up as I started to moan, making her look at me, then smile with her eyes as she saw I was getting close. A second later, she pulled her mouth off me and got on top of me as I stared at her in disbelief.

“Wait, you want it in you?” I asked as she lined me up to her backdoor. “Oh okay, I thought you were going to piss off mom by getting pregnant.”

“I’m not suicidal.” She said as she push me in her quickly, making me moan, then come on the spot from her warmth.

“Damn, you were that close?” She asked. “I barely got the whole five inches in.”

"You measured me?" I asked, making her giggle as she nodded and held up her hand that looked about five inches.

A second later, she started to bob on me, making me grunt and moan from the feeling.

“Well this isn’t my thing.” She said with a whine. “I wonder if it’s yours.”

“Yes, I like it.” I moaned, then she pulled out.

“Not what I meant.” She said, then pulled out the strapon.

I stared at it, then took a deep breath as I turned over, making her put on the toy as I stared at the huge ass dildo nervously. Once she had it on, she looked at my face, then started to hesitate, making me grab my warming massaging lotion that I stole from my dad. She smiled and shook her head.

“Don’t let me use up all your stuff.” She said, then got over me, making me tense up, then she spread my cheeks open as I felt a gust of air just before I felt her start licking my backdoor.

“Oh god, I thought that would be a turn off.” I moaned, making her giggle as she started to push in.

I squirm from the feeling, then grunted with moans. A minute later, I felt myself relax, making her stop, then get over me. I took a deep breath as I felt the toy move past my cheeks, then I let out a grunt as I tried not to scream from the toy tearing me open. I clinched the bed as I moaned, then she stopped.

“I’m sorry.” She yelped, but I grabbed her arms and pull them out from under her, making her slam all eight inches into me as I let out a low moan with a gasp.

“Why did you do that?” She cried. "That's hurting you!"

“It feels good too.” I moaned.

She sighed and pulled off her shirt as I stared at her through my wall mirror. She glanced up as she saw me staring, then smiled as she saw my face.

“You seen me before, haven’t you?” She asked as she flaunted them off by holding them in her hands, that looked to be perfect fit in her palms

I smiled as I liked that, making her giggle.

“That's next, let me pleasure you first.” She said and started to fuck me, making me moan in pain as I buried my face into my bed.

“Is it too much?” She asked, making me shake my head, then grab her hands and placed them on my body.

Taking the hint, she started to massage my body as she kissed my face, then the pain stopped, making me relax as I closed my eyes.

“Are you ready for your squishy softballs?” She asked a few minutes later, making me giggle as I nodded.

She pulled out of me as I looked at her in the mirror, then she looked at me in worry, making her spread my ass cheeks.

“I’m okay.” I said.

“No your not, I ripped you open with this.” She said.

“I don't care, it felt good.” I said, making her look at the mirror and sighed as she nodded.

I turned over without her getting off me fully, making my flagpole stand tall before her. She smiled as she saw that, then reached into the box and pulled out a condom.

“Thank you for that.” I said. “I’m not ready for that kind of trouble.”

“Me too.” She said as she put it on me, then lined herself up to me before looking at me.

I nodded and she pushed me in her, making me grunt and thrust deeper as I grabbed her ass, then started to fuck her just from the feeling of her on me.

“Finally you took charge.” She said.

“More like reacted.” I moaned. “Now my softballs please.”

She smiled and laid down on me as she started bob on me while I started to suckle her nipples.

“Well I know I'm going to like having a child now.” She moaned.

“Not going to happen.” I said in a warning tone. “That’s where I draw the line.”

She nodded with a smile, then started pull away her breasts as she moved her mouth to mine. I opened my mouth, making her lock lips with me. A second later, she pushed her tongue in my mouth, making me suck on it, then she started to moan.

“Brace yourself, I hear that this is the best feeling ever for a man.” She grunted, then started to fuck me faster.

I stared out as she pushed me in her as far as she could, then moaned as I felt several squirts of warm liquid on my balls as her wall clamped down on me, making me gasp as it did feel great and nearly put me over the edge. I push her off me and pull off the condom, just to put it in her ass. She yelped out from the intrusion as I started to fuck her hard from the loss of the edge, making her let out a long moan.

“This feels so much better then when I was doing it.” She moaned. “Cum in me little brother.”

Not to long after, I granted her wish as I pushed myself as far as I could in her and came deep, making a chill ran through her body.

“Wow, what a feeling.” She moaned. “If you can fuck more, then go on ahead, I’m on empty.”

I fell off her with a moan in response.

“You too?” She asked with a smile, then kissed me. "Maybe in an hour. I'm so going to enjoy taking advantage of this new side of you."

**Author's Note:**

> Please give me a Kudos at bottom of the screen if you liked this story. I boosts my confidence that my novels will be liked once i get them published and it aslo boost my mood when I see them, thanks a bunch for reading.


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